Pickpocket

Often found in big cities among bustling crowds, Pickpockets are there, scoring for their own gain. Some may have a moral code to only steal from those who could afford it, but some may just be in it for numero uno. From quick pocket grabs to high scale heists, these rogues have one thing in mind: how much money? Some use their abilities to help themselves to the contents of treasure vaults or uncover hidden secrets, others become an integral part of an adventuring party that values skillful infiltration techniques, and still others get the jump on their foes by taking the fight to them where and when they least expect it, up to and including private bed chambers or inner sanctums. You'll likely end up someplace you're not supposed to be, but those are the places most worth visiting!

Street Magician

Starting at 3rd level, you gain proficiency in the Sleight of Hand skill if you don’t already have it. Your proficiency bonus is doubled for any ability check you make that uses that proficiency.

Additionally, you gain advantage on Sleight of Hand checks to pickpocket, stow an object,  or throw an object as long as at least two of the three following conditions are met: 

• You are in an area with at least 10 people nearby
• The mark is distracted
• You are in stealth

Expert Profiling

At 3rd level you gain the ability to tell who's a bigger score. If you observe a crowded area, for example a bar, you can make an Investigation check to tell a few different things:

• Who would be the easiest to steal from
• Who would be the hardest to steal from
• Who would provide the biggest score

Upon doing this, you may assign someone as a Mark. A Mark has disadvantage on perception checks made to notice your presence, which could make for an easy score. In combat, you may assign someone as a Mark as a bonus action. This not only gives them disadvantage on perception checks made to notice your presence, but additionally missed ranged attacks don't give you away to the Mark. The Mark also takes an additional d6 of damage when you hit with a sneak attack. When the Mark dies, you may use a bonus action to transfer Mark status to another enemy.

Heist Master

Starting at 9th level, your experience has made you apt at strategizing infiltration plans. Whenever you spend at least 1 hour examining a building from the outside, or 10 minutes if you can get the blueprints of a building, whenever in that building you can let a number of allies up to your Intelligence modifier (minimum of 1) to use your stealth modifier for the duration of occupation. If the building is related to a Mark in some way, then the number of possible allies affected by stealth doubles.

Additionally, you learn how to use tools to their fullest potential. You may use thieves tools to craft either a forgery kit or disguise kit. Additionally, you may use your thieves tools for 1 minute to craft a set of climbing equipment in order to scale buildings. As long as the surface is not completely flat you will have a climbing speed equal to half your walking speed. You may use the tools for 10 minutes to craft expert climbing equipment, as long as the surface is not completely flat, you will have a climbing speed equal to your walking speed. If it is flat, it will be half your walking speed. If you use a forgery kit for one minute, you can craft a fake document that would contest a targets Perception, DC 15, to see if its fake or not. If you use a forgery kit for 10 minutes, you craft a fake ID, and supporting documents to contest a targets Perception, DC 20, to see if its fake. If you use a disguise kit for one minute, you can craft a dingy costume that would make you look like a regular loiterer. If you use a disguise kit for 10 minutes you could craft a costume of a worker or member of whatever the building promotes. 

Escape Artist

Starting at 13th level, you know that pride comes before the fall, so you have mastered the art of running away. When an attack misses you, you can use your reaction to move your speed away, and opportunity attacks are made at disadvantage. If a Mark misses you, you may use your reaction to kick around them, jump over them, etc. You can move your full movement, the Mark takes 1d4 plus dex bludgoning damage, and they cannot use their reaction until the start of your next turn. 

Additionally when running away from pursuing enemies, they have disadvantage on all attacks and if you can break line of sight, you have advantage on a stealth check to hide.

All According to Plan

At 17th level, you have taught your crew all they need to know for future marks and scores. You may switch your order in initiative with any willing ally at the start of combat.

Additionally, you may now have two Marks up at a time, and as a reaction, when an ally strikes a mark, you may add your sneak attack damage on to that hit, so long as you haven't used your sneak attack yet.